#------------------------------------------------------------------------------
#$Date: 2020-04-04 06:24:41 +0200 (Sat 04 de Apr de 2020) $
#$Revision: 250097 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/81/4038124.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038124
loop_
_publ_author_name
'Wössner, Jan S'
'Esser, Birgit'
_publ_section_title
;
 Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the
 π-Subsystems on the Optoelectronic Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5048
_journal_page_last               5057
_journal_paper_doi               10.1021/acs.joc.0c00567
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C H2 Cl2, C33 H18 O4'
_chemical_formula_sum            'C34 H20 Cl2 O4'
_chemical_formula_weight         563.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3479(8)
_cell_length_b                   17.257(3)
_cell_length_c                   28.107(4)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.406
_cell_measurement_theta_min      2.372
_cell_volume                     2594.0(7)
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            34844
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.185
_diffrn_reflns_theta_min         1.385
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1407 before and 0.0485 after correction. The Ratio of minimum to maximum transmission is 0.9321. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_recrystallization_method
'The material was recrystallised from CHCl2 by slow evaporation'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 2633 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         8789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0649P)²+1.4038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                7572
_reflns_number_total             8789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           esser_jw283_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_original_cell_volume        2593.9(6)
_cod_database_code               4038124
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.0067(2) 0.18485(5) 0.62813(3) 0.0407(2) Uani 1 1 d . . . . .
O1 O 0.3672(3) 0.52642(9) 0.67324(6) 0.0103(3) Uani 1 1 d . . . . .
C1 C 0.0346(4) 0.60738(12) 0.61680(8) 0.0090(4) Uani 1 1 d . . . . .
Cl2 Cl 0.3208(2) 0.22757(5) 0.54811(4) 0.0430(2) Uani 1 1 d . . . . .
O2 O -0.0756(3) 0.52250(9) 0.68200(6) 0.0107(3) Uani 1 1 d . . . . .
C2 C 0.0153(5) 0.68356(12) 0.59533(8) 0.0098(4) Uani 1 1 d . . . . .
C3 C 0.1745(5) 0.70811(13) 0.55756(8) 0.0114(4) Uani 1 1 d . . . . .
H3 H 0.299453 0.673983 0.545819 0.014 Uiso 1 1 calc R . . . .
O3 O 0.0935(4) 0.58661(10) 0.76551(7) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.1488(5) 0.78141(13) 0.53773(8) 0.0134(4) Uani 1 1 d . . . . .
H4 H 0.259666 0.797583 0.513258 0.016 Uiso 1 1 calc R . . . .
O4 O 0.0276(4) 0.37217(10) 0.67166(6) 0.0153(4) Uani 1 1 d . . . . .
C5 C -0.0415(5) 0.83222(13) 0.55375(8) 0.0139(5) Uani 1 1 d . . . . .
H5 H -0.062848 0.881332 0.539028 0.017 Uiso 1 1 calc R . . . .
C6 C -0.1957(5) 0.81043(13) 0.59068(9) 0.0121(4) Uani 1 1 d . . . . .
H6 H -0.323578 0.844686 0.601074 0.015 Uiso 1 1 calc R . . . .
C7 C -0.1661(5) 0.73715(13) 0.61355(8) 0.0105(4) Uani 1 1 d . . . . .
C8 C -0.3041(5) 0.71764(13) 0.65540(8) 0.0114(4) Uani 1 1 d . . . . .
H8 H -0.428374 0.752202 0.666918 0.014 Uiso 1 1 calc R . . . .
C9 C -0.2590(5) 0.64945(14) 0.67921(9) 0.0118(4) Uani 1 1 d . . . . .
H9 H -0.339792 0.639067 0.708628 0.014 Uiso 1 1 calc R . . . .
C10 C -0.0908(4) 0.59480(13) 0.65937(8) 0.0093(4) Uani 1 1 d . . . . .
C11 C 0.1917(5) 0.54494(12) 0.59560(8) 0.0095(4) Uani 1 1 d . . . . .
C12 C 0.3605(5) 0.50654(12) 0.62467(8) 0.0097(4) Uani 1 1 d . . . . .
C13 C 0.5344(5) 0.45067(13) 0.60799(8) 0.0119(4) Uani 1 1 d . . . . .
H13 H 0.650221 0.427098 0.629145 0.014 Uiso 1 1 calc R . . . .
C14 C 0.5315(5) 0.43134(13) 0.56029(8) 0.0132(4) Uani 1 1 d . . . . .
H14 H 0.651259 0.395751 0.548206 0.016 Uiso 1 1 calc R . . . .
C15 C 0.3501(5) 0.46438(13) 0.52898(8) 0.0117(4) Uani 1 1 d . . . . .
C16 C 0.3382(6) 0.44090(14) 0.48015(8) 0.0155(5) Uani 1 1 d . . . . .
H16 H 0.457758 0.405221 0.468114 0.019 Uiso 1 1 calc R . . . .
C17 C 0.1541(5) 0.46967(14) 0.45029(9) 0.0165(5) Uani 1 1 d . . . . .
H17 H 0.148446 0.453959 0.417912 0.020 Uiso 1 1 calc R . . . .
C18 C -0.0255(5) 0.52254(14) 0.46811(8) 0.0144(4) Uani 1 1 d . . . . .
H18 H -0.154187 0.540983 0.447747 0.017 Uiso 1 1 calc R . . . .
C19 C -0.0157(5) 0.54769(13) 0.51491(8) 0.0115(4) Uani 1 1 d . . . . .
H19 H -0.137006 0.583468 0.526159 0.014 Uiso 1 1 calc R . . . .
C20 C 0.1746(5) 0.52049(13) 0.54644(8) 0.0105(4) Uani 1 1 d . . . . .
C21 C 0.1566(5) 0.49873(12) 0.69987(8) 0.0095(4) Uani 1 1 d . . . . .
C22 C 0.2109(5) 0.53135(13) 0.75052(8) 0.0113(4) Uani 1 1 d . . . . .
C23 C 0.4182(5) 0.49234(14) 0.77663(8) 0.0133(4) Uani 1 1 d . . . . .
C24 C 0.5327(5) 0.52985(16) 0.81445(9) 0.0187(5) Uani 1 1 d . . . . .
H24 H 0.476810 0.579817 0.823836 0.022 Uiso 1 1 calc R . . . .
C25 C 0.7335(6) 0.49382(18) 0.83924(10) 0.0225(6) Uani 1 1 d . . . . .
H25 H 0.811318 0.519907 0.865059 0.027 Uiso 1 1 calc R . . . .
C26 C 0.8149(6) 0.42170(18) 0.82605(10) 0.0232(6) Uani 1 1 d . . . . .
H26 H 0.949928 0.398497 0.842770 0.028 Uiso 1 1 calc R . . . .
C27 C 0.7009(5) 0.38083(16) 0.78768(9) 0.0178(5) Uani 1 1 d . . . . .
C28 C 0.7809(5) 0.30530(16) 0.77390(10) 0.0209(6) Uani 1 1 d . . . . .
H28 H 0.917102 0.281790 0.790094 0.025 Uiso 1 1 calc R . . . .
C29 C 0.6645(6) 0.26578(15) 0.73758(10) 0.0208(5) Uani 1 1 d . . . . .
H29 H 0.721973 0.215744 0.728686 0.025 Uiso 1 1 calc R . . . .
C30 C 0.4588(5) 0.29969(14) 0.71340(9) 0.0175(5) Uani 1 1 d . . . . .
H30 H 0.375674 0.271441 0.689077 0.021 Uiso 1 1 calc R . . . .
C31 C 0.3781(5) 0.37360(13) 0.72497(8) 0.0125(4) Uani 1 1 d . . . . .
C32 C 0.1680(5) 0.40874(13) 0.69778(8) 0.0113(4) Uani 1 1 d . . . . .
C33 C 0.4982(5) 0.41633(14) 0.76241(8) 0.0134(4) Uani 1 1 d . . . . .
C34 C 0.0560(8) 0.2541(2) 0.58261(12) 0.0374(8) Uani 1 1 d . . . . .
H34A H -0.091762 0.258523 0.561572 0.045 Uiso 1 1 calc R . . . .
H34B H 0.085725 0.305407 0.597306 0.045 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C21 113.87(18) . . ?
C2 C1 C11 121.9(2) . . ?
C10 C1 C2 117.8(2) . . ?
C10 C1 C11 120.24(19) . . ?
C21 O2 C10 118.33(18) . . ?
C3 C2 C1 122.5(2) . . ?
C3 C2 C7 118.6(2) . . ?
C7 C2 C1 118.9(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 120.5(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C7 C2 119.0(2) . . ?
C6 C7 C8 121.5(2) . . ?
C8 C7 C2 119.4(2) . . ?
C9 C8 C7 120.8(2) . . ?
C8 C9 C10 119.3(2) . . ?
C1 C10 O2 120.1(2) . . ?
C1 C10 C9 122.8(2) . . ?
O2 C10 C9 116.7(2) . . ?
C12 C11 C1 118.5(2) . . ?
C12 C11 C20 117.7(2) . . ?
C20 C11 C1 123.8(2) . . ?
O1 C12 C13 118.0(2) . . ?
C11 C12 O1 118.1(2) . . ?
C11 C12 C13 123.8(2) . . ?
C14 C13 C12 118.5(2) . . ?
C13 C14 C15 120.6(2) . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 C20 120.2(2) . . ?
C16 C15 C20 119.3(2) . . ?
C17 C16 C15 120.7(2) . . ?
C16 C17 C18 119.9(2) . . ?
C19 C18 C17 120.8(2) . . ?
C18 C19 C20 120.9(2) . . ?
C15 C20 C11 118.8(2) . . ?
C19 C20 C11 122.8(2) . . ?
C19 C20 C15 118.4(2) . . ?
O1 C21 C22 102.13(18) . . ?
O1 C21 C32 106.39(18) . . ?
O2 C21 O1 114.30(17) . . ?
O2 C21 C22 112.76(19) . . ?
O2 C21 C32 108.28(19) . . ?
C32 C21 C22 112.83(18) . . ?
O3 C22 C21 120.2(2) . . ?
O3 C22 C23 124.6(2) . . ?
C23 C22 C21 115.18(19) . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 C33 120.5(2) . . ?
C33 C23 C22 119.8(2) . . ?
C23 C24 C25 120.3(3) . . ?
C26 C25 C24 120.3(3) . . ?
C25 C26 C27 121.2(3) . . ?
C26 C27 C33 119.1(3) . . ?
C28 C27 C26 122.0(3) . . ?
C28 C27 C33 118.9(3) . . ?
C29 C28 C27 121.3(2) . . ?
C28 C29 C30 120.1(2) . . ?
C31 C30 C29 120.6(3) . . ?
C30 C31 C32 119.3(2) . . ?
C30 C31 C33 120.4(2) . . ?
C33 C31 C32 120.3(2) . . ?
O4 C32 C21 120.9(2) . . ?
O4 C32 C31 124.1(2) . . ?
C31 C32 C21 114.6(2) . . ?
C23 C33 C31 122.6(2) . . ?
C27 C33 C23 118.5(2) . . ?
C27 C33 C31 118.8(2) . . ?
Cl2 C34 Cl1 111.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C34 1.783(4) . ?
O1 C12 1.408(3) . ?
O1 C21 1.434(3) . ?
C1 C2 1.450(3) . ?
C1 C10 1.389(3) . ?
C1 C11 1.491(3) . ?
Cl2 C34 1.776(4) . ?
O2 C10 1.403(3) . ?
O2 C21 1.401(3) . ?
C2 C3 1.425(3) . ?
C2 C7 1.435(3) . ?
C3 C4 1.389(3) . ?
O3 C22 1.217(3) . ?
C4 C5 1.417(4) . ?
O4 C32 1.225(3) . ?
C5 C6 1.378(4) . ?
C6 C7 1.427(3) . ?
C7 C8 1.429(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.418(3) . ?
C11 C12 1.386(3) . ?
C11 C20 1.448(3) . ?
C12 C13 1.419(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.429(3) . ?
C15 C16 1.432(3) . ?
C15 C20 1.435(3) . ?
C16 C17 1.386(4) . ?
C17 C18 1.416(4) . ?
C18 C19 1.386(3) . ?
C19 C20 1.429(3) . ?
C21 C22 1.558(3) . ?
C21 C32 1.555(3) . ?
C22 C23 1.490(3) . ?
C23 C24 1.387(4) . ?
C23 C33 1.436(3) . ?
C24 C25 1.423(4) . ?
C25 C26 1.370(5) . ?
C26 C27 1.425(4) . ?
C27 C28 1.425(4) . ?
C27 C33 1.434(4) . ?
C28 C29 1.376(4) . ?
C29 C30 1.419(4) . ?
C30 C31 1.385(3) . ?
C31 C32 1.488(3) . ?
C31 C33 1.437(4) . ?
